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Influence of Molecular Structure on the Biodegradability of Naphthenic Acids

机译：分子结构对环烷酸生物降解性的影响

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Large volumes of toxic aqueous tailings containing a complex mixture of naphthenic acids (NAs; C_nH_(2n+Z)O_2 are produced in northern Alberta by the oil sands industry. Because of their persistence and contribution to toxicity, there is an urgent need to understand the fate of NAs under a variety of remediation scenarios. In a previous study, we developed a highly specific HPLC-high resolution mass spectrometry method for the analysis of NAs. Here we apply this method to determine quantitative structure-persistence relationships and kinetics for commercial NAs and NAs in oil sands process water (OSPW) during aerobic microbial biodegradation. Biodegradation of commercial NAs revealed thatthe mixture contained a substantial labile fraction, which was rapidly biodegraded, and a recalcitrant fraction composed of highly branched compounds. Conversely, NAs in OSPW were predominantly recalcitrant, and degraded slowly by first-order kinetics. Carbon number (n) had little effect on the rate of biodegradation, whereas a general structure-persistence relationship was observed indicating that increased cyclization (Z) decreased the biodegradation rate for NAs in both mixtures. Time to 50% biodegradation ranged from 1 to 8 days among all NAs in the commercial mixture, whereas half-lives for OSPW NAs ranged from 44 to 240 days, likely a result of relatively high alkyl branching among OSPW NAs. It is anticipated that these data will facilitate development of strategic solutions for remediating billions of cubic meters of OSPW stored, or predicted to be generated, in Northern Alberta.
机译：油砂工业在艾伯塔省北部生产出大量含有环烷酸（NAs; C_nH_（2n + Z）O_2的复杂混合物的有毒尾矿，由于其持久性和对毒性的贡献，迫切需要了解修复方案中NAs的命运。在先前的研究中，我们开发了一种高度专一的HPLC-高分辨率质谱法来分析NAs。在这里，我们将这种方法用于确定商业化的定量结构-持久性关系和动力学有氧微生物降解过程中油砂处理水中的NAs和NAs，商业NAs的生物降解表明混合物中含有大量不稳定组分，该组分迅速被生物降解，难降解部分由高度支化的化合物组成。主要是顽固的，并通过一级动力学缓慢降解，碳数（n）对速率的影响很小生物降解，而观察到一般的结构持久性关系，表明增加的环化（Z）降低了两种混合物中NA的生物降解率。在商业混合物中所有NA中，达到50％生物降解的时间为1至8天，而OSPW NA的半衰期为44至240天，这可能是OSPW NA之间较高的烷基支化度的结果。预计这些数据将促进战略解决方案的开发，以补救在艾伯塔省北部存储或预计将产生的数十亿立方米的OSPW。

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